Abstract:

The pseudotrisaccharide allosamidin 1 is a potent family-18 chitinase inhibitor, and it demonstrates biological activities against insects, fungi, and the Plasmodium falciparum life cycle. Compound 1 contains two N-acetylhexosamine residues with the unusual D-allo-configuration and a novel aminocyclitol (i.e. allosamizoline 2), joined by two β-(1→4) glycosidic bonds. Many traditional syntheses of compounds 1-2 and their analogues have been reported. Herein, recent development for the synthesis of compounds 1-2 and their analogues was reviewed. Donohoe and Rosas approach to allosamizoline 2 involves a key-step ring-closing metathesis (RCM) to form the cyclopentene core followed by halocyclization to form the oxazoline unit. Rojas et al. reported that rhodium-catalyzed oxidative cyclization of glucal 3-carbamates led to oxazolidinone-protected mannosamine derivatives. Huang et al. described the solid-phase synthesis of allosamidin 1 and its analogues. The compound 1 and its analogues were obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. Withers and his co-workers research shows that chitobiose and chitotriose thiazolines exhibit chitinase inhibition activity. In a word, the goal is to investigate the novel methods for the synthesis of allosamidin and its analogues, which is convenient for the discovery of allosamidin analogues with high activity.

Abstract: The pseudotrisaccharide allosamidin 1 is a potent family-18 chitinase inhibitor, and it demonstrates biological activities against insects, fungi, and the Plasmodium falciparum life cycle. Compound 1 contains two N-acetylhexosamine residues with the unusual D-allo-configuration and a novel aminocyclitol (i.e. allosamizoline 2), joined by two β-(1→4) glycosidic bonds. Many traditional syntheses of compounds 1-2 and their analogues have been reported. Herein, recent development for the synthesis of compounds 1-2 and their analogues was reviewed. Donohoe and Rosas approach to allosamizoline 2 involves a key-step ring-closing metathesis (RCM) to form the cyclopentene core followed by halocyclization to form the oxazoline unit. Rojas et al. reported that rhodium-catalyzed oxidative cyclization of glucal 3-carbamates led to oxazolidinone-protected mannosamine derivatives. Huang et al. described the solid-phase synthesis of allosamidin 1 and its analogues. The compound 1 and its analogues were obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively. Withers and his co-workers research shows that chitobiose and chitotriose thiazolines exhibit chitinase inhibition activity. In a word, the goal is to investigate the novel methods for the synthesis of allosamidin and its analogues, which is convenient for the discovery of allosamidin analogues with high activity.